1: 450 mg / 85percent H3PO4 / ethanol / 50 h / Heating 2: 350 mg / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / dioxane / 10 h / Heating 3: 120 mg / H2 / Pd-C / ethyl acetate 4: K2CO3 / acetone / 5 h / Heating View Scheme

1: 450 mg / 85percent H3PO4 / ethanol / 50 h / Heating 2: 350 mg / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / dioxane / 10 h / Heating 3: 120 mg / H2 / Pd-C / ethyl acetate 4: K2CO3 / acetone / 5 h / Heating 5: AlCl3 / nitrobenzene / Ambient temperature View Scheme

1: 450 mg / 85percent H3PO4 / ethanol / 50 h / Heating 2: 350 mg / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / dioxane / 10 h / Heating 3: 120 mg / H2 / Pd-C / ethyl acetate 4: AlCl3 / nitrobenzene / Ambient temperature View Scheme

1: 54 percent / I2; pyridine / 9 h / 120 °C 2: 95 percent / H2 / Pd-C / dimethylformamide / 20 °C 3: 53 percent / pyridine / 3 h / 20 °C View Scheme